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Synthesis 2011(10): 1547-1554  
DOI: 10.1055/s-0030-1259983
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I) Iodide Catalyzed Synthesis of Quinolinones via Cascade Reactions of 2-Halobenzocarbonyls with 2-Arylacetamides

Liangbing Fua,b,1, Xiaoli Huanga,b,1, Deping Wanga,b, Pinghua Zhaoc, Ke Ding*a
a Laboratory of Regenerative Biology, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kai Yuan Road, Science Park, Guangzhou 510530, P. R. of China
Fax: +86(20)32015299; e-Mail: ding_ke@gibh.ac.cn;
b Graduate School of Chinese Academy of Sciences, Chinese Academy of Sciences, No. 19 A Yuquan Road, Shijingshan District, Beijing 100049, P. R. of China
c GAC ChangFeng Motor Co. Ltd, YongZhou Branch, No. 68 Liebao North Road, Lengshuitan, Yongzhou, Hunan 425100, P. R. of China
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Publication History

Received 13 February 2011
Publication Date:
01 April 2011 (online)

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Abstract

An efficient copper-catalyzed method for the synthesis of quinolinones, pyridinones, and heteroannulated pyridinones via cascade reactions of substituted 2-iodo-, 2-bromo-, and 2-chlorobenzocarbonyls with 2-arylacetamides is reported. The protocol works well for the reaction of most of the 2-iodo-, 2-bromo- and 2-chlorobenzocarbonyls with 2-arylacetamides.

Key words

copper iodide - diamines - cascade reactions - amidation - quinolinones

    References

  • 2a Chung HS. Woo WS. J. Nat. Prod.  2001,  64:  1579 
    Google Scholar
  • 2b Ito C. Itoigawa M. Furukawa A. Hirano T. Murata T. Kaneda N. Hisada Y. Okuda K. Furukawa H. J. Nat. Prod.  2004,  67:  1800 
    Google Scholar
  • 2c He J. Lion U. Sattler I. Gollmick FA. Grabley S. Cai J. Meiners M. Schünke H. Schaumann K. Dechert U. Krohn M. J. Nat. Prod.  2005,  68:  1397 
    Google Scholar
  • 3a Oshiro Y. Sakurai Y. Sato S. Kurahashi N. Tanaka T. Kikuchi T. Tottori K. Uwahodo Y. Miwa T. Nishi T. J. Med. Chem.  2000,  43:  177 
    Google Scholar
  • 3b Xiao Z. Waters NC. Woodard CL. Li Z. Li P.-K. Bioorg. Med. Chem. Lett.  2001,  11:  2875 
    Google Scholar
  • 3c Chilin A. Marzano C. Guiotto A. Baccichetti F. Carlassare F. Bordin F. J. Med. Chem.  2002,  45:  1146 
    Google Scholar
  • 3d Buchstaller H.-P. Siebert CD. Steinmetz R. Frank I. Berger ML. Gottschlich R. Leibrock J. Krug M. Steinhilber D. Noe CR. J. Med. Chem.  2006,  49:  864 
    Google Scholar
  • 3e Freeman GA. Andrews CW. Hopkins AL. Lowell GS. Schaller LT. Cowan JR. Gonzales SS. Koszalka GW. Hazen RJ. Boone LR. Ferris RG. Creech KL. Roberts GB. Short SA. Weaver K. Reynolds DJ. Milton J. Ren J. Stuart DI. Stammers DK. Chan JH. J. Med. Chem.  2004,  47:  5923 
    Google Scholar
  • 4a Sliskovic DR. Picard JA. Roark WH. Roth BD. Ferguson E. Krause BR. Newton RS. Sekerke C. Shaw MK. J. Med. Chem.  1991,  34:  367 
    Google Scholar
  • 4b Suzuki M. Iwasaki H. Fujikawa Y. Kitahara M. Sakashita M. Sakoda R. Bioorg. Med. Chem.  2001,  9:  2727 
    Google Scholar
  • 4c Bach T. Bergmann H. Grosch B. Harms K. J. Am. Chem. Soc.  2002,  124:  7982 
    Google Scholar
  • 4d Kumabea R. Nishino H. Tetrahedron Lett.  2004,  45:  703 
    Google Scholar
  • 5a Terpko MO. Heck RF. J. Am. Chem. Soc.  1979,  101:  5281 
    Google Scholar
  • 5b Jia C.-S. Dong Y.-W. Tu S.-W. Wang G.-W. Tetrahedron  2007,  63:  892 
    Google Scholar
  • 5c Tang D.-J. Tang B.-X. Li J.-H. J. Org. Chem.  2009,  74:  6749 
    Google Scholar
  • 5d Kadnikov DV. Larock RC. J. Organomet. Chem.  2003,  687:  425 
    Google Scholar
  • 5e Kim KH. Lee HS. Kim JN. Tetrahedron Lett.  2009,  50:  1249 
    Google Scholar
  • 5f Marcaccini S. Pepino R. Pozo MC. Basurto S. Valverde MG. Torroba T. Tetrahedron Lett.  2004,  45:  3999 
    Google Scholar
  • 5g Staskun B. J. Org. Chem.  1964,  29:  1153 
    Google Scholar
  • 5h Marull M. Lefebvre O. Schlosser M. Eur. J. Org. Chem.  2004,  54 
    Google Scholar
  • 6a Manley PJ. Bilodeau MT. Org. Lett.  2004,  6:  2433 
    Google Scholar
  • 6b Kadnikov DV. Larock RC. J. Org. Chem.  2004,  69:  6772 
    Google Scholar
  • 6c Cortese NA. Ziegler CB. Hrnjez BJ. Heck RF. J. Org. Chem.  1978,  43:  2953 
    Google Scholar
  • 7a Wang D. Cai Q. Ding K. Adv. Synth. Catal.  2009,  351:  1722 
    Google Scholar
  • 7b Cai Q. Wei J. Fu L. Pei D. Ding K. Org. Lett.  2010,  12:  1500 
    Google Scholar
  • 7c Chen H. Wang D. Wang X. Huang W. Cai Q. Ding K. Synthesis  2010,  1505 
    Google Scholar
  • 7d Cai Q. Li Z. Wei J. Ha C. Pei D. Ding K. Chem. Commun.  2009,  7581 
    Google Scholar
  • 7e Li Z. Fu L. Wei J. Ha C. Pei D. Cai Q. Ding K. Synthesis  2010,  3289 
    Google Scholar
  • 7f Zhou J. Fu L. Lv M. Liu J. Pei D. Ding K. Synthesis  2008,  3974 
    Google Scholar
  • 8a Wall M. J, Player M. R, Patch R. J, Meegalla S, Liu J, Illig C. R, Cheung W, Chen J, and Asgari D. inventors; PCT Int. Appl.  WO 2005009967. 
  • 8b Wajon JFM. Arens JF. Recl. Trav. Chim. Pays-Bas  1957,  76:  65 
    Google Scholar
  • 8c Blackburn TP. Cox B. Guildford AJ. Le Count DJ. Middlemiss DN. Pearce RJ. Thornber CW. J. Med. Chem.  1987,  30:  2252 
    Google Scholar
  • 8d Bergman J. Brynolf A. Vuorinen E. Tetrahedron  1986,  42:  3689 
    Google Scholar
1

These two authors contributed equally to this work.